For years, booking a trip has meant thinking like a database: dates, budget, star rating, distance from the beach. Tick the boxes, sort the results, hope the photographs are honest. Davide Bertolino tried something different.
With a few days spare at the end of an Italian trip last year, he opened ChatGPT and described the kind of trip he was in the mood for. Normally, the traveler does the translating, turning a vague idea of the trip they want into the narrow set of fields a booking engine understands. Bertolino skipped that step and he wasn’t disappointed with the results.
I hadn’t simply asked for a destination, a four-star hotel, a pool and a certain price. I had described how I wanted to feel.” That is the direction of travel for AI: a technology that can read the vibe a traveler is chasing, not just the price, the dates and the star rating. Bertolino, who still uses conventional booking sites, sees the two as doing different jobs.
AI can sometimes understand something much less measurable: the atmosphere and sensations I’m looking for.” “AI is already moving the experience away from forms, filters and rigid searches toward conversational commerce, where travelers can simply describe the outcome they want, the kind of trip they want to take, their budget or even how they’re feeling, and have AI help guide them toward the best options,” Andrew Jordan, chief technology officer at Travelport, told Newsweek. The integration of AI into travel represents a shift toward meeting travelers’ needs rather than simply delivering search engine-optimized results. Agentic AI will finally give them one,” Ilan Twig, co-founder and CTO of Navan, said.
But AI is also transforming travel behind the scenes, in ways most travelers never see—from shaping the vacations they consider to identifying problems and finding solutions at airports and during flights. While AI may help, it isn’t able to deliver the first-hand knowledge that dedicated travel experts can provide, warns Joe Cronin, president of International Citizens Insurance. Google Flights and AI trip planners are great at finding the cheapest fare or building a day-by-day itinerary.
However, they consistently miss the risk element. They won’t tell a traveler that their credit card’s travel coverage excludes adventure sports, or that a ‘flexible’ fare still leaves them exposed if a hurricane cancels their whole trip,” Cronin said. Frequent travelers have opted to use heavily integrated AI solutions to common travel burdens, as a companion to an airline app.
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